#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023845.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023845
loop_
_publ_author_name
'Myra Beaudoin Bertrand'
'Joshua D. Neukom'
'John P. Wolfe'
_publ_section_title
;
 Mild Conditions for Pd-Catalyzed Carboamination of N-Protected
 Hex-4-enylamines and 1-, 3-, and 4-Substituted Pent-4-enylamines.
 Scope, Limitations, and Mechanism of Pyrrolidine Formation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8851
_journal_page_last               8860
_journal_paper_doi               10.1021/jo801631v
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C17 H17 N O'
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.6260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9786(7)
_cell_length_b                   9.4279(6)
_cell_length_c                   13.7572(9)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      23.33
_cell_measurement_theta_min      2.41
_cell_volume                     1288.01(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART-APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31655
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2007/4) Bruker AXS area
  detector absorption and other corrections, University of
  Gottingen, Germany 2007.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.3801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                2974
_reflns_number_total             3220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801631v_si_003.cif
_cod_data_source_block           mbb203
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023845
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.72084(8) 0.87067(8) 0.50861(6) 0.01784(18) Uani 1 1 d . . .
O1 O 0.68905(7) 1.10306(7) 0.47624(5) 0.02163(17) Uani 1 1 d . . .
C1 C 0.75065(9) 1.00804(10) 0.52371(6) 0.01639(18) Uani 1 1 d . . .
C2 C 0.61184(10) 0.82455(11) 0.43656(8) 0.0233(2) Uani 1 1 d . . .
H2A H 0.6320 0.8473 0.3693 0.028 Uiso 1 1 calc R . .
H2B H 0.5251 0.8688 0.4488 0.028 Uiso 1 1 calc R . .
C3 C 0.60947(11) 0.66456(11) 0.45338(8) 0.0264(2) Uani 1 1 d . . .
H3A H 0.5771 0.6135 0.3927 0.032 Uiso 1 1 calc R . .
H3B H 0.5514 0.6398 0.5052 0.032 Uiso 1 1 calc R . .
C4 C 0.75709(11) 0.62986(10) 0.48494(8) 0.0231(2) Uani 1 1 d . . .
H4A H 0.8109 0.6277 0.4282 0.028 Uiso 1 1 calc R . .
H4B H 0.7660 0.5376 0.5193 0.028 Uiso 1 1 calc R . .
C5 C 0.80023(9) 0.75272(10) 0.55389(7) 0.01788(19) Uani 1 1 d . . .
H5A H 0.7719 0.7331 0.6203 0.021 Uiso 1 1 calc R . .
C6 C 0.94818(9) 0.79366(10) 0.56209(7) 0.0190(2) Uani 1 1 d . . .
H6A H 0.9733 0.8102 0.4944 0.023 Uiso 1 1 calc R . .
C7 C 0.96385(9) 0.93397(10) 0.61673(7) 0.01780(19) Uani 1 1 d . . .
C8 C 1.07846(10) 0.96391(12) 0.68234(7) 0.0233(2) Uani 1 1 d . . .
H8A H 1.1491 0.8963 0.6915 0.028 Uiso 1 1 calc R . .
C9 C 1.08878(10) 1.08907(12) 0.73271(7) 0.0249(2) Uani 1 1 d . . .
H9A H 1.1671 1.1071 0.7760 0.030 Uiso 1 1 calc R . .
C10 C 0.98571(10) 1.19219(11) 0.72193(7) 0.0212(2) Uani 1 1 d . . .
C11 C 0.99442(11) 1.31993(12) 0.77729(7) 0.0264(2) Uani 1 1 d . . .
H11A H 1.0712 1.3370 0.8223 0.032 Uiso 1 1 calc R . .
C12 C 0.89378(11) 1.41810(12) 0.76646(8) 0.0267(2) Uani 1 1 d . . .
H12A H 0.9009 1.5033 0.8035 0.032 Uiso 1 1 calc R . .
C13 C 0.77931(11) 1.39326(11) 0.70045(7) 0.0238(2) Uani 1 1 d . . .
H13A H 0.7090 1.4615 0.6939 0.029 Uiso 1 1 calc R . .
C14 C 0.76798(10) 1.27147(10) 0.64537(7) 0.0197(2) Uani 1 1 d . . .
H14A H 0.6902 1.2570 0.6008 0.024 Uiso 1 1 calc R . .
C15 C 0.87091(9) 1.16681(10) 0.65408(6) 0.0174(2) Uani 1 1 d . . .
C16 C 0.86406(9) 1.03587(10) 0.60088(6) 0.01598(19) Uani 1 1 d . . .
C17 C 1.03802(11) 0.67524(11) 0.60713(9) 0.0283(2) Uani 1 1 d . . .
H17A H 1.0246 0.6654 0.6764 0.042 Uiso 1 1 calc R . .
H17B H 1.1325 0.6983 0.6007 0.042 Uiso 1 1 calc R . .
H17C H 1.0147 0.5859 0.5732 0.042 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 122.05(8) . . ?
C1 N1 C5 124.32(8) . . ?
C2 N1 C5 113.36(8) . . ?
O1 C1 N1 121.81(8) . . ?
O1 C1 C16 123.35(8) . . ?
N1 C1 C16 114.83(8) . . ?
N1 C2 C3 102.26(8) . . ?
C2 C3 C4 103.04(8) . . ?
C3 C4 C5 102.61(8) . . ?
N1 C5 C6 108.60(7) . . ?
N1 C5 C4 101.71(7) . . ?
C6 C5 C4 116.75(8) . . ?
C5 C6 C7 108.03(7) . . ?
C5 C6 C17 111.86(8) . . ?
C7 C6 C17 114.07(8) . . ?
C16 C7 C8 119.07(9) . . ?
C16 C7 C6 119.17(8) . . ?
C8 C7 C6 121.75(9) . . ?
C9 C8 C7 120.79(9) . . ?
C8 C9 C10 121.53(9) . . ?
C9 C10 C11 121.38(9) . . ?
C9 C10 C15 118.91(9) . . ?
C11 C10 C15 119.71(10) . . ?
C12 C11 C10 120.70(10) . . ?
C11 C12 C13 120.01(9) . . ?
C14 C13 C12 120.83(10) . . ?
C13 C14 C15 120.94(9) . . ?
C14 C15 C10 117.81(9) . . ?
C14 C15 C16 123.86(8) . . ?
C10 C15 C16 118.30(9) . . ?
C7 C16 C15 121.28(8) . . ?
C7 C16 C1 118.15(8) . . ?
C15 C16 C1 120.53(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3404(12) . ?
N1 C2 1.4640(12) . ?
N1 C5 1.4681(12) . ?
O1 C1 1.2362(11) . ?
C1 C16 1.4970(12) . ?
C2 C3 1.5266(15) . ?
C3 C4 1.5297(15) . ?
C4 C5 1.5319(13) . ?
C5 C6 1.5194(13) . ?
C6 C7 1.5219(13) . ?
C6 C17 1.5249(13) . ?
C7 C16 1.3855(13) . ?
C7 C8 1.4141(13) . ?
C8 C9 1.3672(15) . ?
C9 C10 1.4125(15) . ?
C10 C11 1.4230(14) . ?
C10 C15 1.4253(13) . ?
C11 C12 1.3631(17) . ?
C12 C13 1.4075(16) . ?
C13 C14 1.3742(13) . ?
C14 C15 1.4208(14) . ?
C15 C16 1.4333(12) . ?
